


Blue Eyes and Black Ties

by castielismybabydaddy



Category: Supernatural
Genre: BDSM, Boss!Dean, Bottom!Gabriel, F/F, F/M, Fear, Light BDSM, M/M, Office Sex, Public Sex, Rape/Non-con Elements, Sub!Castiel, Top!Sam, bottom!Castiel, castiel is forced into submission, dom!Dean, started in an elevator, top!dean
Language: English
Status: In-Progress
Published: 2016-05-02
Updated: 2016-05-02
Packaged: 2018-06-05 19:52:17
Rating: Mature
Warnings: Graphic Depictions Of Violence, No Archive Warnings Apply, Rape/Non-Con
Chapters: 10
Words: 12,676
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6720586
Author URL: https://archiveofourown.org/users/castielismybabydaddy/pseuds/castielismybabydaddy
Summary: <blockquote class="userstuff">
              <p>Castiel Novak is a hard worker but one day his pride gets the best of him after his boss Dean Winchester embarrassed him infront his coworkers.<br/>It is only him and his boss late at night and Castiel decided to give him a few words only for it to blow up in his face.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> So this story will have some triggers but not so early in the story. I will post triggers in every chapter's summary so readers will be warned about what they need to prepared to read.  
> Give me feedback and please kudos!!

Castiel groaned at the seemingly never ending pile of work his boss dropped on his desk. A repeated snap of fingers brought his dulling blue eyes to meet Dean Winchester's sinfully green ones.

 

"I need these done by 9 am tomorrow." Dean announced with a fake smile plastered on his face. Castiel glared at the pile.

 

"Mr. Winchester, that means I have to stay late." Castiel deduced, looking up to see Dean scoff at him.

 

"What do you do after work that is so important?" Dean asks sarcastically. "You stay as late as I tell you to."  Dean glared at him. Smile still there. Castiel realized the office was quiet when he could hear his blood pulse in his ears as he got more and more anxious. "But Mr Winchester. My sister is having a baby shower tonight and she hasn't been in the city in two-" an ominous chuckle interrupted Castiel, his face burning with embarrassment.

 

"Clarence. I want these papers filed by 9 am tomorrow," Dean repeated lowly, "or you're fired." With that Dean Winchester walked off. Dangerous dominance radiating off every inch of his body. Castiel saw some women flinch as he walked by. Nobody dared to move or speak until the only elevator doors on the floor closed.

 

"Cassie? Are you okay?" Charlie Bradbury, Castiel's one of many friends at the office, asked pulling him into an awkward hug. "Yeah," he shrugged sadly, "let me just... Call Anna and tell her that I won't make it."

 

Charlie let him go and gave him a  
encouraging pat on the back before returning to her own cubicle.

 

It's going on 11 and he still hasn't come closed to finishing. Anna sent Castiel pictures of the shower, and told him that it was okay that she understood his predicament. He complimented the baby clothes and told her to save him a slice of the belly shaped cake before getting back to work.

 

After the last of the strays left the office around 12, Castiel decided to lay back a while. He only had a quarter left to finish, thank god.

 

Castiel leaned forward laying his face on his arms. "Fucking hate this job," he muttered, light tears bled into his sleeves.

 

Sadly this was all Castiel could do. Complain. In the end, he knew if he ever wanted to survive in this world he must suck it up and deal with the fact he's got it good.

 

It's just rewriting the same damn thing on hundreds of paper for his douchebag of a boss.

 

Castiel realized after grading another paper that the almighty Dean hasn't left the office yet. Which is weird since he usually leaves right before Castiel does at 8:30. And it's just going on one.  
He didn't see the man leave and the elevator only goes through this floor to the main desk. Castiel would have notice Dean leave because he glared at the elevator doors all day.

 

Suddenly, the most off the wall thought made Castiel stand up and march to the elevator. He mashed the up button and crossed his arms with determination because he was going to give Mr. Winchester a piece of his mind. There aren't any workers around Dean could embarrass him in front of and the worst thing that could happen was he would get fired. Not that he actually cared anymore. His brother would take him into his corporation in a heart beat but his pride made him say no to start with.

 

He boldly stepped into the elevator but his confidence started to deteriorate as each level came and passed on the dial.

  
Castiel silently prayed to the Gods that he gets to Dean's office and not be face to face with him as the ding signals to him that he has reached his floor.

 

Sadly, the Gods decided to ignore him and the one and only Dean Winchester was suited up and waiting for the doors to open.

 

Dean glared at Castiel, and crossed his arms as the cubicle coworker left the elevator and stood in his personal space.

 

"What the hell do you think you're doing?" Dean's eyes never left Castiel's, "Why are you in my elevator, on my floor, in my face?"

 

As Dean spoke his voice rise with anger And if possible got closer.

 

"Mr. Winchester," Castiel began, instinctively looking away as he spoke to his boss. "I did not appreciate how you handled me and my business earlier," his voice broke as Dean smirked.

 

"Is that so?"

 

Dean shoved Castiel back into the elevator pressing him harshly into the bar in the back. Dean's hot breath against his throat and hands gripping his arms tightly made Castiel shiver.  
"How do you want me to handle you now?" He asked, skimming his nose across Castiel's collarbone.

 

"You come into my elevator to give me a piece of your mind like a naughty boy. You tell me I didn't handle you properly."

 

Castiel huffed, thankful when Dean pulled back but fear engulfed him when he saw his bosses green eyes dark and dangerous.

 

"How should I, the boss, handle you, the worker?" His nails dug into Castiel's arms.

 

"Don't. No. This wasn't what I meant." Castiel struggled to get away but Dean firmly brought his hands up to Castiel's shoulders and forced him to kneel.  
"Then what did you mean?" A smile played on Dean's lips.

 

Castiel didn't say anything. He will refuse to speak. It has only got him in trouble today and not talking might save him from getting raped right now.  
Dean pressed a button on the pad that made the elevator stop.

 

The world froze.

 

Maybe it won't.

 

Dean forced him to look up at him. Castiel couldn't swallow it it would choke him from how far he had his neck strained.

 

"What did you mean?" Dean repeated his grip on Castiel's jaw tightened so much Castiel's sight was starting to blur from suffocation.

 

"I-I do-n't... Know," Castiel whimpered,  his hands shot up to loosen Dean's hand on his throat. Instinct telling him to fight off his attacker, but he knows he can't.

 

"What's your name." Castiel held back a scoff. He's been working for Dean Winchester for almost 4 years and he is asking his name.  
"Cas-gah-stiel Novak.." He was thankful Dean finally let him fall back. Castiel swallowed air like it was water, his heart pounded and Dean just glared at him.

 

"Castiel.. I want to see you in my office first thing in the morning," he picked his briefcase back up and started the elevator again. Before the door opened Dean spared him one last look.

 

"First thing in the morning," with that he was gone.

 

Fear pulsed in Castiel veins. What did he get himself into. He stood on shaky legs, shocking himself that he even made it to his cubicle.  As he finished the last of the papers he couldn't stop a few from getting tear stained.

 

At 3:37, Castiel finally clocked out.

 

At 3:46 Castiel made it to his apartment.

 

And at 6 am his alarm went off telling Castiel that he didn't get any sleep and he has only two hours to prepare for what sinful punishment Dean Winchester has in store for him.


	2. Chapter 2

Castiel rolled onto his back to smack the alarm clock silent. His breath shuddered on the way out. It was one thing to be ready for being fired, but this is different. Dean didn't even say anything about packing his things. Just to be there at the office first thing. What happened last night made him want to curl into a ball from shame and fear that what Dean has in store for him is going to be a lot like last night.

Castiel closed his eyes trying to lull himself for the thousandth time to sleep. He'd rather not go in today. He just needs to sleep.

Charlie's Star Wars ringtone blared into the previously silent room.

Well there went that idea.

He shuffled to the dresser to answer the damn call.

"What Charlie?" He heard a strained chuckle on the other line.

"Castiel freakin Novak, Care to explain why Bossy Mc-Scared-Me-Straight came up to me and told me to let Castiel Novak know to meet him in his office when he got here?" Charlie hissed into the receiver.

"I'll tell you when I leave his office," Castiel murmured. He could hear the impatience in her voice as she ended the call with clipped conversation and a 'get your ass here ASAP'.

  
It just hit 7:30 and Castiel was standing awkwardly out side of the office building. Anxiety flooded his veins, causing a feathering heat to speed up his heart rate.

Castiel stared up at the building, his eyes lingering in the 7th floor where Dean's office was.

Taking a deep breath Castiel's shake hands pushed through the main entrance, his trembling less forced him past his and Charlie's cubicles, and took all Castiel had left to press two little buttons separating him and his Boss.

He stepped up to Mr. Winchester's assistants desk, ignoring the side glance she gave him as she left him sitting on his sofa in the office.

"Mr. Winchester will be with you in a moment," her dainty voice did nothing to sooth the knot in his stomach.

Long minutes passed by with Castiel listening to the offbeat of his heart and tapping his fingers in tune to a internal lullaby on repeat.

You're okay. Castiel assured, it's not gonna be that bad.

The door swung open and Deans loud laugh brought Castiel out his reassuring bubble. Dean didn't even acknowledge the man sitting on his couch, instead he made a bee line to his desk and sat talking to his Bluetooth ear piece.

"Don't worry Zach it will be done. Tell the wife I said hello," a pause "Alright I'll see you tomorrow."

It was quiet. The only thing Castiel focused on was the fabric of his dress pants.

Dean cleared his throat causing Castiel to jump slightly. He didn't dare to lift his blue eyes.

"Mr. Novak," Dean's voice was low and husky, and it made Castiel's palms sweat but he didn't answer.

Dean stood and made his way over to Castiel stopping only a foot away.

"Mr. Winchester," Castiel said finally. He was so proud of himself that his voice didn't crack.

"Have you thought of how I should punish you for last night?"

Straight to it then.

Castiel shook his head, he only thought about rape. He thought of all the scenarios that will all lead up to him doing what ever Dean asked. He thought about how much it shocked and scared him knowing he wouldn't try to stop Dean if he ever tried to take him.

But Dean couldn't know that.

"Do you wanna here my idea?" Castiel mentally smacked himself for popping a semi. Why is he such a masochist?

Hesitantly, Castiel nodded.

Dean suddenly crouching in front of Castiel made him flinch, his face was close and mischief played in the green of Dean's eyes.

"Well, you can apologize to me, replace my assistant, and you will do everything I tell you, when I tell you without a word," Dean paused smiling a little at his next thought, "or you can apologize to me now, I punish you for your stunt, and you continue working on level one. The catch? I will call you up here and teach you lessons on how to be obedient at different times on different days, while you do the walk of shame all the way to my elevator as all your coworkers look at you with confusion and-if anyone finds out- perhaps disgust." He clucked his tongue. His eyes taking in Castiel's stoic expression.

Castiel thought hard. Charlie would tell him to run. That it's not worth it to stay.

But he missed a touch of a lover even if he won't admit it. He missed being told he was a good boy and being praised for doing good. Or punished for being bad. That's why he won't fight and Dean probably knows it. He could probably see it. The way Dean is going he might be perfect despite the situation and his previous anger toward his boss.

About what Dean said, he'd rather leave a group of confused workers on the first level and work a few yards away instead of staying and feeling their heavy gazes locked on him every time Dean called for him.

"I'll be your assistant."

Dean smiled at him, a full smile, a proud smile, and stood.

"That's great, first thing you will do as my assistant," he tilted Castiel's head up with a finger, "get on your knees and give me a proper apology." Dean took a step back and waited.

Castiel took another deep breath, slid off the sofa onto the floor, and dropped his head.

"Mr. Winchester, I'm-"

Dean tsked, "don't tell me with words," his hand massaged himself through his slacks, "show me you're sorry."

A blush heated Castiel's cheeks.

Castiel scooted closer, nimble fingers unhooked the belt slowly, then undid his pants.

No shame

No shame

Castiel tucked Dean's underwear under his ballsack before taking hold of his cock. Even soft it was lengthy. It didn't even take long for Castiel to get it thick and heavy.

He pressed kisses to the tip, muttering apologies before licking strips down to the base. Castiel parted his lips, taking Dean in.

Soft, still, suckles turned into deep thrusts and mild gagging. He moaned around Dean's cock earning a gravelly groan in response.

Deans fingers knotted in Castiel's short, raven locks so he can keep him still as he pushed in deep enough to tickle Castiel's nose with his golden curls.

Over and over for what felt like forever, Castiel couldn't keep the tears from falling and Dean never let up.

Castiel finally felt Dean's hips stutter before his come shot down his throat.

He slid off of Dean. He sat jaw slack panting hard. Sporting a hard on in his own slacks.

Deans hand patted his cheek and Castiel looked up.

"Apology accepted."

Dean pulled the kerchief from his jacket pocket, cleaned himself off, and tucked his dick back into his briefs.

"I'll have Ms. Milton pack her things and you yours and you can switch later on today," Dean helped Castiel off the ground, "You may go."

Castiel left the office imagining a wrinkled old lady in a string bikini and tattoos, and it helped make his dick flaccid. He walked into the men's room near the elevator, and observed his features.

His lips were plump and bruised, and his eyes were teary and swollen.

He can't go down there now Charlie will notice even if he keeps his head down she will notice something was different.

He washed his face and thought of a story to tell Charlie why his face was swollen.

**Notes for the Chapter:**

> Wooooh I finished the second chapter!!! Thanks for your comments I appreciate them and I hope you like this chapter.
> 
> Maybe it was a little too early for porn but I couldn't think of anything else to do.


	3. Chapter 3

**Notes for the Chapter:**

> This is a fuller chapter that gives us Charlie's insight of the situation. Enjoy.

He stood in the elevator and practiced the story before pressing the button to the first floor.

The doors open to a low roar of murmurs and taps on computers, and Castiel's eyes sought out his best friend, happy that she was making her way towards him.

"Cas have you been crying?" Charlie asked, pulling him into a hug once she was close enough.

"What did he say," Garth called out he was also worried. Castiel looked around the room, locking eyes with everyone in the room. This was it.

"Uh.. He.. Mr. Winchester is promoting me to his... Assistant." He dropped his eyes at the harsh intake of breath by several people.

Charlie groaned angrily, "Castiel what did you do!?" She lifted his head. Her eyes searching and it didn't shock him that she found something. Her eyes thinned and she dragged him toward the girls bathroom.

Hushed whispers didn't miss his ears and he knew that they knew Charlie found something too.

She pushed him into the bathroom and locked the door, turning around and getting in his face in the same breath of time.

"What happened in that office." She gritted, observing his face once more making sure she didn't miss anything. It would be useless to lie and she is waiting to call out another bluff.

"Last night..." She crossed her arms, waiting, "after everyone left, I had been alone with my thoughts and after a while I decided to give Dean what's what."  
Castiel covered his face with his hands and huffed a frustrated laugh. "I came face to face with him on his floor and..."

Charlie hugged him again, "And what?"

She patted his shoulder to get him out of his thoughts. "And he turned it around. Pressed me against the bar, made me kneel. Charlie, he made me kneel!"

She sucked in a breath,"Castiel, that's-" Castiel held up a hand, "don't say it, because I know."

He picked at the hem of his sleeve. "Today, he.. He, um.. Punished me for going into his elevator," Castiel could feel her shock seep into his skin.

"He.. I might let him be my new Dom... Charlie..." He looked into a stall ignoring her gaping mouth.

"What do you mean!?!" She whispered harshly, "Just last week we were eating cake and talking shit about what we want to do to him because he is a douchebag!"

"You don't think I don't know that!" Castiel whispered back just as angrily, "You think I planned to be a submissive little bitch to my own boss? I would rather sit on needles for a day!" He growled, she just stared at him apologetically.

She waited till his breath evened and it didn't sound like he was gonna cry before speaking.

"I'm sorry Cassie. Look on the bright side," she said, rolling her eyes at his glare, "now that you are going upstairs you can be fucked when ever, and I know how much you missed that." A slap in the arm made her chuckle.

"If he ever goes past your limits, you better tell me and then I will actually beat the shit out of him." Castiel nodded.

He sighed, " Can you help me pack my things? He wants me up there today."

Charlie still had an unsure look, but she agreed anyway. They left the bathroom and everyone was still waiting with concern.

"It's alright everybody," Charlie announced, "He will tell you when it is the right time. Today is just not that time."

Castiel was happy no one pushed him while he and Charlie packed his things. Kevin even joked with him about this being the last time he had to look at Castiel's mug, and it's hard to get anything, especially a joke, out of Kevin.

Ms. Milton's heels clacked out of the elevator, and everyone looked up. She held her head high with a smile as she made her way toward Castiel and Charlie, who was putting the last of his things in his box.

"Mr. Novak, Mr. Winchester wants you up there pronto," her smile held secrets and it creeped him out.

"Well I just finished packing," he began, "so I'll just head up there," he stared awkwardly at her undying smile.

Charlie gave him one last hug, "I'll see you after work," she said after him. He stepped in the elevator, accepting all the motivating glances from his now old coworkers.

-

Castiel set his box on the empty black desk. He ran a nervous hand through his hair, and began to unpack quickly.

He placed his laptop last on his desk and stepped back to admire his new organized desk. A small smile played on his lips before he remembered who he was a assistant for.

A ring from the phone on his desk also reminded him.

"Hello?"

"Great your here! Come into my office." Dean's voice echoed into the receiver.

"Yessir," then a click to signal that he was just hung up on.

Castiel pushed through the doors and walked to Dean's desk. Dean was holding out a packet.

"These are the instructions, what you will do, as my assistant," Dean said expectantly. His green eyes locked with Castiel's blue ones.

"Yes sir," Castiel murmured, taking the packet and looking through it. To his surprise they were all work related. He closed the packet and waited to be dismissed.

It never happened. Instead Dean pointed to the ground, "Kneel."

Castiel set the packet on the desk and lowered to his knees, slowly.

"Tell me something," Dean huffed, "why are you here?"

Castiel looked up, with confusion. Why was he asking that?

"Because you told me to come in here Mr. Winchester," he answered hesitantly.

"Yes I did," he smiled lightly.

"Let's get one thing straight, Castiel," Dean got up and walked around his desk to get in front of Castiel for the second time that day, "You agreed to work as my assistant," he knotted his fingers in his hair and pushed Castiel's face against his groin, "you will do everything I tell you or face the consequences."

  
Castiel's muffled "yes sir" did not go unnoticed.

Dean let go, patted him on the cheek, walked back around his desk, and sat down.

"You may go."

Castiel stood as fast as his shaky legs would let him and left, too wrecked to risk looking back.

He needed relief but he knows he won't get it from Dean anytime soon. He sat down gingerly, trying to avoid any brushes or tug of his slacks that would make him harder than he'd rather be.

_You masochist!_

For the next few hours, Castiel sat waiting for any new errands or activities Dean wanted him to do. There was a few coffee runs as well as another quick blowjob by the time Dean needed to leave. Not that Castiel was complaining.

It could be worse.

When Castiel got home he brushed his teeth. Again. Again. Each time cursing himself because the memory of Dean Winchester's cum refused to leave his taste buds.

A knock on his door intruded his self disgust.

Oh yeah! Charlie said she was going to come over after work.

"What's up bitch!" She said when he opened the door. She paraded through the house stoping only to get his icecream and two spoons, before burrowing herself into his couch.

"How was the first day of rape work?"

He laughed joining her on the couch, "Eh, a little less rapey then I expected but it was okay," he muttered nonchalantly.

"How many times?" She dipped her spoon into the tub.

"Twice," her spoon dropped.

"I'm sorry, did you just say that Dean Winchester fucked you twice. On the first day?" Her voice got progressively louder with each syllable.

"No, no," he waved her off blushing hard. Castiel wouldn't be this calm if Dean fucked him today, even if he had been expecting it.

"He fucked my mouth twice." He pointed to his lips as he spoke.

"Did he make you-"

"Swallow it? Yeah," he shuddered at the sudden warm in his stomach, "and let me tell you,he isn't a soft shooter."

She mocked a gag, "That is disgusting-" pause for effect, "-ly hot."

"Charlie you're not supposed to be into this!" He laughed taking a bite of icecream.

"Oh?"

"Don't you 'oh' me." He continued, taking another large scoop of icecream out of the tub and shoving it his mouth.

**Notes for the Chapter:**

> Isn't charlie amazing? I tried to make her a little more against it but they're best friends. Charlie's down for what ever Castiel wants. CX
> 
> ALSO!! I will be making the next chapter in Dean's third person POV so you guys can see what's going on with his life.
> 
> Thank you for reading! Comments and questions are welcome.


	4. Days

**Summary for the Chapter:**

> Dean is ready. Castiel is willing

**Notes for the Chapter:**

> I apologize for the long wait. I will be adding chapters all week

 

If there is anything to be confused about. It should be about how easy Cas let Dean do what he did.

 

Does Dean feel bad? No. Should he? Maybe. Is he going to continue forcing his cock down the bitch's throat? You know it.

 

Dean stood by his living room window and watched the world from up high, thinking, planning. Tomorrow will be a better day.... More controlled.

 

****

 

Dean proudly pushed through the front entrance, nodding toward every hesitant Good morning Mr. Winchester only to stop at Mrs. Milton's -used to be Castiel's- desk.

 

"Good morning Mr. Winchester," Milton said flirtatiously. His answering smile made her giggle.

 

"Did you get what I asked you to last night?" He leaned on her desk lightly.

 

"Already on his desk and stamped fragile, handle with care." Milton replied quickly. Her smiled softened and Dean gave her a pat on the shoulder.

 

"Perfect. Thank you." With that he was gone, nodding one last time to Ms. Bradbury before stepping into the elevator.

 

It wasn't until halfway up he realized Ms. Bradbury was smirking. That made him angry. Did Novak tell everyone anyway? Or does Bradbury know something that Dean didn't.

 

  
Dean tensed his face and walked out of the elevator. Novak was sitting at his desk the package nowhere in sight.

 

Hm. Interesting.

 

Dean walked pasted him slowly and stopped before entering his office.

 

"Did I receive anything this morning?" Dean smirked slightly at the prominent blush on Castiel's cheeks.

 

"Yessir , I opened it and it is stationed on your desk." Castiel replied, wringing his fingers underneath his desk anxiously.

 

"Perfect, be in my office in approximately 30 minutes. We have work to do."

 

Castiel's nod had gone unnoticed as Dean pushed through his doors.

 

Dean chuckled at how neatly folded the whip was on his desk. Underneath was a cock cage and a blue vibrating butt plug. Perfect.

 

Thirty minutes later Castiel eased into the room, hands behind his back and eyes on the floor.

 

"What's the work sir?"

 

"Did you like what was in the box?" Dean asked a small smirk played on his lips. The contents haven't left their place on the desk so the amount of amusement Dean got watching Castiel blush as he observed the objects more closely gave him the utmost feeling of lust.

 

"Please. Lets get started," Dean stood removing the whip from the desk.

 

"Strip. Then on your knees, Mr. Novak"

 

Dean waited until Castiel had kneeled a good while before speaking again.

 

"Ms. Bradbury gave me some risky looks as I was coming up. Would you care to explain that?"

Dean held his gaze as he brushed the fabric across Castiel's bare leg, his dick, then back over his other leg.

Castiel didn't dare flinch so early into the scene.

"I don't know.. Sir." Castiel whispered, his mouth fell open with minor need.

Dean loved this. He could have had this a long time ago.

"I'm sorry kitten. That's not the answer I was looking for."

Dean lifted his armed hand and struck Castiel on both of his thighs. The tense hiss he let out made Dean's cock twitch.

"Tell me. Why was Bradbury so smug?" Dean straightened up to undo his slacks.

"She.. Um she.." Castiel stutters, eyes never leaving Dean's crotch.

"She knows that I get your cock."

Dean chuckles lowly.

"You get my cock? Hmm?" Dean forced Castiel to look him in the eye.

"Did you tell her how much of a weeping bitch you are? Hmm? Or his your mouth begs to taste my cock?"

Castiel nodded. He brings his hands up toward Dean's calves.

"I told her how I'm just a little slut for your cock sir." Castiel groaned.

Dean licks his lips at the sight of Castiel's growing erection.

"I'm going to fuck you Novak. And you are going to fucking love it." Dean's growls.

  
"But first. You need to be well restrained. Stand up an walk with me."

Dean picks up Castiels fallen tie and fastens it around his mouth. They walk towards the desk, Dean reaches for the cock cage and vibrator.

This is going to be hot.

**Notes for the Chapter:**

> Soooooo so soooooo sorry. I haven't been able to update for months!!
> 
> Well this one is back on track as will be my other ones thank you!!!
> 
>  
> 
> How about it huh? Dean's a feisty one ain't he.


	5. Sir

  
Castiel was kneeling on Dean's desk, legs spread and cock heavy. With his arms bound behind him and being gagged, Castiel did nothing but breath.

 

Dean circled him smiling wider than ever.

 

"Oh Castiel," Dean stopped in front of him, vibrator in hand, "how nice you look. So beautiful."

 

Dean gave Castiel a pat in the cheek before walking around to the front of the desk, behind Castiel.

 

Castiel sat still, hearing lids pop open and close in a span of ten seconds. Cold fingers breached his hole. A muffled grunt escaped his throat.

 

He hasn't done this in a long time, it wasn't shocking that he had to be stretched out.

 

One finger. Two. As Dean slipped the third finger past his brim Castiel was shaking and moaning as loud as a tie could let him be. Shaking so bad the desk was wobbling with him.

 

Dean must not of mind because he never let Cas rest. Ignoring Castiel's cries and pumping and twisting his fingers faster and faster until Castiel was edging and orgasm.

 

Suddenly fingers were gone and a deep rumble invaded Castiel's space.

 

The vibrator slid in easily, settling snugly next to the bundle of nerves that makes Cas go crazy.

 

"Ugh!?" Castiel wanted to cry, wanted to be released, but at the same time he wanted more. Needed more.

 

"You're doing great, Castiel," Dean murmured pulling the vibrator out only to push it back in even slower.

 

"I wanna hear your pretty little screams. Wanna feel you around me," Dean licked up his spine pulling the vibrator out all the way this time and turned it off.

 

"Think it's my turn?" Dean teased, letting the suspense nip at Castiel's body.

 

"Humph?" Castiel felt the blunt tip of what he assumed was Dean's cock press into him.

 

"Take it all in one go," Dean commanded taking Castiel by the throat and thrusting his thick cock deep into him.

 

He didn't wait for Castiel to get use to his girth. Dean ripped himself out just as easily as he shoved in.

 

Castiel squealed with shock. Nononono! Stop no please! He patted his hand three times as a warning. This was not making him happy. He was too full, he bets if he was able to touch he would feel Dean through his stomach.

 

He wanted to be warm and held right as Mr. Winchester fucked him through and through. He didn't want to be raw and aching at the end of this.

 

Dean took a hint and tugged the tie out of Castiel's mouth.

 

"Speak," Dean growled, not slowing his pace. He tilted his hips slightly, searching for that pressure point just for Castiel.

 

"Ah! P-please! Sl-oh fucking god!! D-ammit slow d-ow! Down!!" Castiel cried out trying and failing to keep Dean in the pulling out position.

 

Dean grunted, pulling all the way out and flipping Castiel on his back.

 

"Is this what you want?" Dean was in between Castiel's legs again burrowing deep once more. He began lazily thrusting into the man, tilting his hips this way and that until he found it.

 

Castiel flinched with pleasure. Yes this is better.

 

Castiel, slack jawed and panting, nodded, wishing his hand weren't tied at the moment. He wanted to feel Dean, to memorize his body with his fingers.

 

"Dean please," Castiel whispered, lustful eyes search for understanding.

 

Dean placed his arms tight around Castiel's lower back, and pulled out enough that only the tip was in.

 

"Correct yourself," Dean demanded.

 

Castiel nodded muttering apologies.

 

"Sir,"

 

"Yes?"

 

"Fuck me?"

 

Dean didn't answer with words, instead his body finished the conversation.

 

Many would say this position is too intimate for first time "relations", but Castiel didn't care. He was being watched by his boss as he got fucked slow and hard by his boss.

 

  
He hardly had any time to think about the kiss Dean pressed hotly onto his lips. His mouth opened wide, letting Dean lick and feel his whole mouth with his tongue.

 

The intimacy made Cas shiver.

 

He needs to cum. He is a few thrusts away from blowing his load. Cas wasn't going to make it.

 

And he didnt. Untouched and all over Dean's pristine dress shirt, Castiel was left shaking and moaning incoherent things about Dean.

 

Dean stops kissing him and scoffs.

 

Castiel, still in his post orgasm stage, doesn't feel Dean move him to his knees, nor did he realize his legs were shaking like a new born deer.

 

Dean pulled off the condom (that Cas didnt even know was there) and stuffed his cock passed Castiels lips.

 

"You should have waited kitten," Dean chuckled sliding his dick deeper.

 

Castiel gripped Dean's thigh.

 

"Now I have to do it for you."

 

Dean pulled out so Castiel could catch his breath only to shove it deep again and hold it.

 

Castiel understood what was going on. Dean was going to hold his dick inside Castiel's throat as a punishment for Cas not waiting.

 

The problem wasn't the breathing though. Every time Castiel swallows the saliva Dean seems to grow bigger.

 

"Are you ready?" Dean held his head still, so he blinked twice for yes.

 

Dean fucked Castiels throat, and Castiel was gagging so much that he was honesty scared Dean's cock would make him throw up.

 

Not long after Dean shoved in one final time, letting his thick stream into Castiel.

 

Dean untied Castiel's arms and picked the fucked out man up.

 

Castiel held on for dear life, still moaning, still high on arousal.

 

Castiel was carried into Dean's private bathroom and set on the counter.

 

A warm wet towel patted and wiped Castiel's body down.

 

"You did well." Dean murmured lifting Castiel's face with one finger.

 

"Did I hurt you any?" Dean said taking ahold of Castiel's ginger wrist.

 

"O-only when you fucked into me that first time," Castiel answered, "uh everything else was extraordinary."

 

"Sorry, I was in the heat of the moment," he gave a small smile, that could melt anyone's heart.

 

"Can.. Can you um... Kiss me one more time please, sir?" Castiel asked softly, half expecting a laugh in his face.

 

There was no laugh, there was only a smile.

 

"Sure." Dean pressed his lips against Castiel's hesitantly. Castiel opened up slightly as an invitation and was overjoyed that Dean accepted.

 

After the kiss Dean didn't waste any time pampering Cas picking up his clothes and letting him change.

 

"Mr. Novak, see if I have any meetings or appointments for today," Dean said passively.

 

"Yes sir," Castiel nodded making his way toward the door and to his desk.

 

Once seated Castiel felt open. His whole body was electrifying.

This is fine. Everything is fine.

* * *





	6. Dropping

**Summary for the Chapter:**

> Ah yes.. Snuggly sadness for you all

**Notes for the Chapter:**

> Heyyyy sir for the long wait. I got number seven waiting for ya.

As Castiel spent the rest of his morning sitting quietly and waiting for emails of Mr. Winchester's distributors, he thought about all the things that had gone wrong.

He should have just let Dean fuck him from behind. Oh! And how can he forget that he stained Dean's dress shirt?! 

Castiel face palmed. If he doesn't talk to Charlie soon he was going to have a panic attack. Lunch is in an hour, he'll have to wait.

"Mr. Novak?" The intercom in his desk threw him out of his self deprecating thoughts. 

"Uh, yes sir?" 

"I'll need you in my office."

"Hmm. Yes sir."

Castiel stood and pushed through the doors, not expecting to be face to face with Mr. Winchester.

"So, you and I both know that if I just leave you out there you might fall victim to sub drop and that could affect your work," Dean explained calmly.

"So I decided to allow one hour of pampering after a scene," Dean announced lacing his fingers in Castiel's.

He pulled them to the couch, sitting first and tugging Castiel into his lap.

"Castiel, you were good,"Dean began, putting their laced hands in between them.

"But I didn't want you behind, I should have just done it, it didn't feel bad I just don't prefer it," Castiel rambled, "and them I didn't wait for you and got your shirt dirty!"

Castiel teared up lowering his head in shame.

"You have to realize that although you have to do what I say, I will never go over your limits unless I believe you can take it." 

Dean pulled Castiel's head to rest in his shoulder.

"This it the first time so this was an experiment, which is why I didn't use the cock cage. Next time you will take it from behind, you will wear the cage, and you will not cum." Dean confirmed, making Castiel look him in the eye.

"Yes sir," Castiel murmured. 

"As for the kissing...." Dean continued hesitantly, "We are not in a relationship, this is playing by my command, so we will keep the kissing to a extreme minimum. Understand?"

"Yes sir."

"Good. Today was already extra so kissing will be used for this session. Just today's." Dean said, not looking directly at Novak.

Castiel leaned forward and pressed his lips to Dean's, who pushed back with playful dominance. 

For that hour, Dean whispered praises and future ideas to Castiel, making Castiel feel a whole lot better than he did earlier.

When the hour was up Castiel reluctantly removed himself from Dean's lap, giving Dean a unwilling wave goodbye as he left for lunch. 

Charlie was waiting at the base of the elevator, smiling.

"Ready?"

Castiel smiled back, ready to tell her everything.

"Yeah." 

At the restaurant Castiel spilled every bean from the can. From the rough first scene to the cuddles and kisses of aftercare.

"You know what I think," Charlie asked pointing a fry at Castiel's chest.

"What do you think, princess?" Castiel stuffed a few fries in his mouth too.

"Mr. Dickchester might actually be strung on you, I know how that sounds after these three years have been, but what if he realized how great you are only because of your sass?"

Charlie looked so serious it was hard for Castiel no to laugh. 

"Uh. No. He made it very clear he wants me only for my body. Nothing else. Aftercare is supposed to be borderline intimate for emotional reasons." 

Castiel shrugged it off.

"If he wouldn't have done it I would be sitting here crying like a infant because 'he didn't think to remind me as a Dom and Sub that I did good.' When he actually did but I was being dramatic. You know?"

Charlie just nods. "Yeah, destiel is totally fucking canon." 

What is Destiel?!" Castiel glared at his best friend.

"Dean x Castiel equals Destiel," Charlie said bluntly, dodging a salty fry aimed for her face.

"Shut up and just let me enjoy the moment." 

The subject changes shortly after and for the rest of lunch and well as the rest of the day Castiel is left thinking about Dean Winchester.

Dean doesn't try to have any sexual interaction for the rest of the day. Cas is kinda bummed about it, if he is honest with himself.

Even a tease would have been very much okay, but Cas didn't get anything. 

As he got ready to leave for ready he got a text message from Charlie.

LarpQueen: didn't Dickchester leave a while ago?

Me: yeah like 30 minutes ago why?

LarpQueen: he is in front of the building waiting for someone. X/

Castiel hurried to the elevator. Is Dean waiting for him? A smile broke out on his face. 

LarpQueen: mayday DO NOT COME ASSISTANT BITCH AND DICKCHESTER ARE RIDING TOGETHER.

Me: I'm in the elevator what do I do?!?

His heart deflated.

LarpQueen: CLICK THE ELEVATOR STOPPER! HOLY SHIT THEIR LIPS ARE LOCKED!

Castiel slammed his hand on the button and collapsed. His phone dinged three more times by he couldn't gather enough courage to read Charlie's messages. 

He waited for 3 minutes before standing once again, his face dead and emotionless.

LarpQueen: THEY JUST FUCKING LEFT

LarpQueen: you're in the clear

LarpQueen: IMMA BOUT TO FIGHT THAT EQUALLY RED HEADED WHORE!

Me: Charlie calm.

Me: it's alright. Dean's a grown man

Me: used only for body remember.

LarpQueen: oh Cas, you're not a fucking toy! 

Castiel watched as the doors slid open and suddenly his arms were full of a red faced Charlie.

"Let's go," Charlie had a semipermanent scowl etched on her face.

"I swear not much could have changed after lunch," she growled as they walked.

Castiel hasn't said a word, it don't even look like he was ready to even speak for another year.

"He used me Charlie." Castiel whispered.

"What?" Charlie turned around, taking hold of Castiel's arms.

"I said he fucking used me. And me being what I am just let him." Castiel suddenly broke down.

He bawled into Charlie shoulder, only edging her anger further. Her eyes shot open with sudden realization.

"Sub drop!" Charlie exclaimed, "Castiel! We need to get you home in cuddle mode so you won't lose it."

~Dean's third person POV~

Dean glanced at his phone and saw Ms. Milton had sent him a few text about dinner tonight.

He didn't reply. His head was full of the blue eyes sub right outside his door.   
He didn't understand what he was feeling, or why he wanted to full that sub so full of kisses.

He shook his head, he needed a distraction. Milton. She isn't a sub, but she is a switch. She can Dom or one person and sub for the other.

Dean needed to fuck another sub. 

He answered the invite with a yes and a short little idea for afterwards. He collected all his stuff and left his office, sending a curt nod toward Mr. Novak.

Outside, Milton took Dean by the arm and brought him to her car.

"Is everything alright," she asked signaling to the highest floor where Castiel is. 

Dean shook his head and pulled the woman into a deep kiss.

"I need a sub with no boundaries tonight." Dean pulled her closer, smirking with her. 

They got into the car, not knowing that Charlie saw everything and Castiel was dropping.


	7. No should mean no, but i liked it

**Summary for the Chapter:**

> WARNING 
> 
> RAPE\NON CON IS ABOUT TO GO ON.
> 
> ok so i honestly dont know if masochism works this way but cas is a masochist and even though he hated the idea of what's about to go down he ends up liking it.

**Notes for the Chapter:**

> ENJOY
> 
> AND 
> 
> IM SORRY IF IT SUCKS ASS
> 
> LOVE YOU

Castiel didn't go into work the next day.

Or the day after that. 

After succumbing to the fact that he was way too elated by the thought of being a sub for Winchester, he let himself go.

He got four calls from the office, the extension number clearly Dean's but what was he supposed to do? Answer him? Naaahhhhhhh.

He laid in bed, only moving to text Charlie his hourly actions, sometimes missing a text because he was sleeping the days away.

On the third day however, Cas was forced to leave his room because of the violent knocking on his apartment door.

Cas hesitated. There's only three people who would be knocking. 

April, his ex who has been able to find almost every apartment he's ever moved into just to tell him off.

Charlie, who he knows would have texted him before hand but since he didn't check his phone before he left the room it could be a possibility.

And lastly, His boss, Dean Winchester, who might or might not be setting it in stone whether to fire him or not.

He didn't have a peep hole so with blind faith that it was not the last one he slowly opened the door.

"We need to talk," was the first things said as the door was cracked open.

Castiel's hope for heaven's trust buried itself deeper than ever when it was, in fact, Dean Winchester. 

Dean was dressed in one of his many work suits, and his gelled hair and a desperate gaze gave Castiel the thought of a over exaggerating prom date who was left at waiting at the entrance for an hour only for the date to be a no show.

"Sorry I haven't been at work, I've been feeling quite ill," Cas replied going to shut the door only to have Dean push through letting himself in.

"Don't lie to me. Charlie asked to have a meeting, where she spent thirty minutes threatening me." Dean's agitated expression made Cas's stomach queasy.

Castiel didn't say anything. His eyes locked to the ground fearing that if he did say something he would regret it.

"You have no right to act like you own me, Castiel. I'm not your Dom. I'm just a Dom who needed a genuine submissive for the time being."

Castiel's eyes locked with Dean's. shock and, for once in a while, rage burned through his whole body.

Cas shook his head. He can't listen to this garbage. 

"Mr. Winchester, I honestly don't know why you had to confront me about this just to tell me not to act like I own you," Castiel was trembling with rage.

"If anything, I should be asking you why you think you own me," Cas cleared his throat watching Dean's eyes get wider.

"Just like you're not here to be only my Dom, I'm not here to get sexually acquainted with my actual boss just because he is a horny mother fucker who doesn't care about anyone but himself!" Cas was almost screaming now.

Everything went into slow motion, it was like a movie scene cut and slowed down to make every action seem even more real that reality itself.

Dean's fingers were pressed tightly around the base of Castiel's throat as he was pushed further into the apartment. He was stopped by a wall and everything came crashing down on him.

Dean's fingers didn't loosen as hot lips harshly pressed into another's, forced entry with Dean's tongue made Castiel's knees go weak.

Castiel's failed attempts to push Dean away only caused his grip to tighten until the poor boy was left gasping for air.

It wasn't kissing anymore, it was choking. Castiel weakly punched Dean's arm, but nothing worked. The light was fading and his heart beat pulsed his ears until all he could here was the slowing thud before he passed out.

He woke up blindfolded, and he couldn't move anything except his head. Castiel knew he was naked, if the cold air and light breeze between his spread legs was anything to go by.

"Dean?" 

A sharp smack to the leg made Cas scream with fear. Please let this not be..

"Tsk tsk tsk," Dean murmured from farther away, "I only came here to bring you back to the office."

Castiel stayed silent.

"You know I was going to fire Charlie, for having the nerve to even assume the worse of this unfortunate situation," Cas felt The bed dip near his feet, "but I decided against it because she is the best tech supporter we have ever hired."

Castiel's breathing became heavier when he noticed that Dean was crawling over him ever so slowly until he could smell Dean's minty breath.

He held his own not wanting to disturb the stillness between them. 

Castiel flinched as calloused fingers lightly slid up and down his torso. A shuddered breath escaped his throat.

"P-please! Don't do anything!" Castiel whispered, trying to curl away from Dean. 

"Oh honey, you shouldn't have talked back to me," Dean cooed, "this is your punishment."

Castiel shook his head.

"No no no no no!" Castiel cried, his tears leaked out from underneath the blindfold. 

"Oh don't worry Cas, I'll make you feel so much better."

"I'm sorry, please!" Castiel tried and tried. This was not how he wanted to go.

Fingers grazed the inside of his thighs Getting him involuntarily aroused. The soft sensations were multiplied by the loss of his sight.

"So gorgeous," Dean whispered, "all spread out for me to fuck you." He pressed a cool finger into Cas, causing the sobbing submissive's breath to hitch.

Dean didn't waste any time prepping Cas, slowing and speeding his pace just to hear the man moan underneath him.

Cas felt a sudden change. Dean was no longer looking above him, but lifting Castiel's spread legs to thrust his leaking cock into him.

Castiel screamed. The sound would frighten a bear but Dean? No his motives were only fueled by the sexy noise.

He felt so full. 

So needed.

Even though what Dean is doing is wrong, who is he to not enjoy?

Dean fucked into Cas with hardly any mercy but that's what made Castiel's toes curl. The burning pain from inside edged him toward his masochistic orgasm. 

Red faced and panting, Castiel let out a breathy moan the moment Dean's cock hit his prostate. 

Electricity burned through him, and wanted more.

"Ah! Please Dean!" 

A sharp smack to the face caused Cas to cry out with a mixture of lust and shock.

"Correct yourself slut!" Dean growled against his throat, using a strong hand to choke said throat.

"Ack! Sir! Ah I'm sorry!" 

Dean didn't loosen his grip as he thrusted faster into the submissive.

Dean was almost there, he was so closed to cumming inside of this beautiful sub.

Every moan and pleading cry asking him to stop or slow down only egged him to fuck him faster and harder.

Cas was lucky he didn't have Dean's toys.

You see Dean didn't come here to fuck this guy, hell the bonds for his arms were Castiel's shirts and the blindfold was his sleeping mask with cats on it.

He didn't even have a whip to spank this naughty boy.

Dean abruptly pulled out to kneel on Castiel's chest. 

He jerked fast and hard edging his orgasm before finally shooting is load all over Castiel's face.

Rolling his eyes as Castiel came untouched right after him.

Castiel sobbed, trying hard to ignore the drying cum, sweat, and tears on his cheeks.

The pressure of his arms and legs loosened until he was just a aching mess of muscles and bones on the bed. He ripped of the blind fold looking for Dean.

Dean took hold of Castiel's neck once more and yanked him to the end of the bed.

His hands shot up to loosen Dean's hold, and Castiel couldn't believe what happened next.

Their lips met, and to say that it was passionate was an understatement.

It was down right fiery. 

Dean's lips slotted into Castiel's nipping the skin and licking the salty cum of his face.

Castiel moaned; he's never felt so used.

And he fucking liked it.

~~~

**Notes for the Chapter:**

> Soo?
> 
> ....*cricket noises*....
> 
> Yeah I feel ya, I feel ya...
> 
> ....*more cricket noise*....
> 
> So that was your favorite scene? Mine too!!
> 
> ....*cricket noise one more time*....
> 
> Yeh the next chapter won't have smut in it don't worry
> 
> SOOOO thank you for reading this chapter! I hope you liked it, an I'm sorrynotsorry that its most of this story is smut. Sam and Gabe will make a show in this book soon be ready.


	8. Contract for Consent

Castiel's back at work the next day. Sadly.

Dean left him with empty promises and body aches. But it was all right. He will be alright.

Castiel was finishing Dean's schedule for the rest of the week; Dean was currently in a meeting with Kevin Tran discussing who knows what.

Castiel listened to the low murmurs of their voices enjoying the muffled chuckles conjuring from his boss.

He shook his head. No. He can't. Not after what happened yesterday. Even though every bone in his body is begging to forgive, he just can't.

He's become the physical definition of a walking mat, and that hasn't settled in his stomach all to well.

Kevin later walked out with an expectant smile on his face, giving Cas the immpression that he got what he came for.

"Bye Cas," Kevin waved as he stepped into the elevator. Cas waved back, giving a wide smile.

"Mr. Novak, make a meeting for Gabriel Novak tomorrow at 3." Dean said into the intercom. Cas mentally screamed. Abort! He needs a diversion!

"A-um... Sir you scheduled a coffee meeting with Bart from Tech Corp!" He scrambled through his sticky notes making sure he was right.

"Your week is already booked," Cas rushed, slamming the button of the intercom.

"Reschedule it for next week. Its urgent," Dean answered, clearly amused by this reaction.

He is fucking screwed. The moment Gabe sees Dean and THEN finds out Cas is his damn secretary he is going to demand Castiel's transfer.

"Yes sir."

"Uh oh and you're coming."

Fuck him in the ass with a cactus. His long pause made Dean laugh.

"Yes sir."

He picked up the phone on his desk and called Gabriels. Main office number.

"Hello?"

"Hi, yes this is the secretary of Winchester-Singer Inc. requesting a meeting for Dean Winchester to have coffee at 3 tomorrow." Cas pitched his voice higher than normal attempting to mask his voice from his brother.

"May I know the name of the man who figured out the number to my office. Only few have direct access." Cas cringed. He knew that was a mistake.

Fuck his autopilot stress mechanism.

"Its Cas," the laugh he heard from  
brother sounded tense. Its the stiff laugh a dad makes when a girl brings her boyfriend over for the first time. Or that half laugh a mock makes when she overheard some one dissing her snacks.

"Promotion was a secretary position?" Gabe asked, letting Cas grovel in awkward silence.

"More like forced." Cas muttered loud enough for his brother to hear.

"Ill only accept if you are present. We need to have a chat little bro." Gabriel finalized his humored tone no longer honest.

"I will, he said so before I made the call." Cas wrote it in the calendar and sent it to dean via email.

"Alright, Im about to go into a meeting. See you tomorrow little bro."

A click signaled his leave. He leaned back and rubbed his tired face. This is the worst week and a half of his life.

The creak of Deans door opening shocked Cas out of his chair.

"Lets.. Go eat..?" Dean gave a shy half smile that honestly scared the shit out of Cas. Cas just stared at him opened mouthed.

"Like, some hamburgers maybe?" Dean continued sticking a thumb towards the elevator.

"Uh y-yeah. S-sure?" Cas quickly gathered his things and followed Dean to the elevator.

"What's your favorite thing to do after work?" Dean tried, giving Cas a nudge unintentionally also making him flinch.

"Um... I-me and Charlie usually hangout at my house and watch old sifi shows." Cas watches Dean nod and mentally makes a note not to give too much details.

The elevator doors open and Cas follows Dean out of the building, making sure Charlie wasn't having a panic attack watching them go.

Dean leads Cas to his car and sends him off to his home so they can switch out and drive to the restaurant in Dean's car. Cas ran inside real quick to change shirts, ignoring that little voice in his head warning him about Dean's intentions.

"Are you ready?" Dean held the passenger door open and shut it for Cas, confusing the hell our if him.

"What's caused this date, Mr Winchester?" Cas asked, fiddling his fingers to the beat of the sing playing through the sound system.

"My brother actually," Dean glanced at the nervous coworker, who looks too innocent for his previous actions. The way his tousled black locks only seemed to get more messy with each second; his plump, chapped-looking lips that are too tasty for his own good. Dean was riled up the moment he left the office, but Sam suggested to get this lawfully right. With the right morals and utmost persuasion.

First a date with the man. No sex, no matter how tempting it would be to just take it. Sam produced a legal document for his ordeal and, if the date goes well, Cas will sign it and legally become his submissive for a year.

"C'mon, Ellen has been waiting on us for a decade." Dean said putting the car in park and stepping out of the car.

"You're brother?" Cas was quick to follow, "you're brother asked us to go on a date?"

"Kind of, more or less threatening me to stop acting like a Dick." Dean abruptly turn on his heels face not even an inch from Cas's, " I don't know though, it seems to me you like my rough housing. "

Dean turned back around leaving a flustered secretary scrambling to pick up his clammy marbles before following his boss inside.

The food was homey; the cook as well as a few waitresses were flirty. The one Cas liked the most was the daughter of the cook-restaurant owner, Jo Harvelle.

She explained Dean's life story, even the secret story about him trying on one of his girlfriends pink lacy panties and liking it. She saved that one for when Dean went to go use the bathroom.

When he came back though, Cas's face was a borderline burgundy with pink tints around his ears from laughing so hard. Jo shot Dean a protect-this-smol-bean look before taking her leave.

"What's caused this reaction right now?" Dean couldnt help but smile, he sipped his second beer, letting the carbonation distract him from the cute angel in front of him.

"Uhhhh... Vegan jokes," Cas blurted calming his burning cheeks with his suddenly cold hands.

Dean just stared at him, " sorry honey, but this place would be the last a vegan would wanna show up at," Jo let out a hearty laugh at her own joke. Dean was chuckling quietly in front of Cas, who is currently wanting to hide.

After Jo excused herself dean pulled out the folded document and handed it to Cas.

"My brother," Dean began, sliding his finger up and down his cup, "also wanted me to make what we've been doing in our spare time... part of a legal agreement; only for if and when I hurt you, you can choose to leave or stay, and if I ever go past your boundaries- not counting the basic Dom and Sub relationship- you will have the right, if the charge is proven with medical evidence, to sue me for being abusive to a person in your position."

Cas took hold of the paper. "Suing is  a little much don't you think?"

"In most cases its to protect a party of the contract." Cas nodded, even though he would never sue considering the situation.

"Hmm."

Dean leaned forward with a hopeful look, "is it a yes then? Will you sign?"

Cas refused to look desperate so he waited a second before nodding again. Dean's smile grew and pulled out his wallet, throwing a hundred on the table.

"Jo's going to love the tip," Dean muttered practically dragging Cas out of the restaurant. Cas just laughed, sliding into the car easily.

Before Dean started the car, he pulled Cas into a kiss, more as a thank you than anything else. The little grunt Cas made almost made the man giggle like a school girl. 


	9. Winchester

**Summary for the Chapter:**

> Gabriel... what?!?

**Notes for the Chapter:**

> SORRY! I haven't updated in forever.

This emotional roller coaster that Dean is forcing Cas to ride was making him mentally nauseous. They went over the contract at Castiel's house, and when they were done, Dean pulled Cas into another kiss.

He was certain his boss was bipolar. He wasn't asked to commit any acts that night but he was told that he would be the next day.

Cas still had to sit through a meeting with his brother and Dean in the same perimeter. His suit he chose was covering. He put on a full three piece and a trench coat just so his brother wouldn't think the immediate worse of this situation.

His morning consisted of a surprise visit to be picked up by Dean, and a cup of coffee, in exchange for a kiss and an early morning prepping for a vibrator that will stay in until Dean said otherwise.

Dean was forcing himself to just prep Cas, although the soft grunts and pleas for more only edged him to destruction.

"Cas, baby, stop squirming," Dean cooed as he pulled into the parking lot of their workplace, "You got to act indifferent or people will find out."

Dean smiled at Cas's low whimper. He wondered if Cas was regretting wearing all those layers. Dean walked in first, nodding towards all the good mornings being murmured to him by his employees. He caught Charlie's eye and gave a small smile before heading into the elevator.

Cas on the other hand waited a good five minutes before entering, rearranging himself in his slacks. When he stepped through the doors Charlie was there in a flash.

"What did he do?" She checked him for injuries, which made him hold in a laugh.

"Nothing Charlie. He took me on a date?" Cas cocked his head at the memory.  Small smile graced his lips.

"The Dean Winchester, took you on a date?" Charlie gasped, her expression was full blown curiosity. "Was it like-"

"An actual date? Yes." Cas finished taking ahold of her hand. "I met his second mother and his kind of sister."   
Charlie gaped at him.

"Wow, when is he going to pop the question?" This time Cas was the flustered one. He stood straight, and dropped her hand.

"Don't say things like that." He shook his head, not wanting to get hopeless feelings thinking about stuff like that.

What if Dean asked him THE question. He would feel guilty for hating him most of the time. Even now he doesn't understand how after four years he would suddenly fall in love with his boss just because he was forced to spend more time with him.

It's like his life is a crazy drama.

"You said date.. mother... and sister... He's never taken anyone anywhere but his place to bang." Charlie stated pointing a sharp nailed finger at him.

"I know, I've been here a long time Charles." He rolled his eyes. "So that means he must be really ready."

Cas pulled her to the entrance of the elevator. "All he wanted me for after the date was to sign a contract for that kind of thing, Charlie. I don't think he wants anything like that."

"Well I'll see you after work? We have a date for the movies after. Remember?" Charlie said pushing him into the elevator.

"Yeah, I remember just meet me after work, I didn't drive," Cas glanced up.

"Bye!"

"Bye Charlie."

The elevator door closed, and he pressed the seven button. Suddenly a sharp vibration crippled his body. He sucked in a breath and cried softly. The elevator doors opened and he was able to stumble through the floor and to his desk without falling out.

Dean was in his office, a small remote in his hand when Cas pushed the door open, falling on his knees just as fast.

"What took you so long?" Dean rolled his chair back, watching the man on the floor.

"The highest setting does not disappoint me," Dean laughed out, standing up and walking around Cas.

"Face to the floor," Dean commanded, humming in with approval when his was immediately obeyed.

What Cas was not prepared for was the foot that pressed the vibrator deeper into him. The repeating pressure made his toes curl.

He couldn't scream. He involuntarily pressed back into Dean's foot. His body begging to be defiled, only to be let down for the umpteenth time.

Dean stepped back, turning the vibrator all the way off, and just watched Cas tremble and whine on the floor.

"Sit up."

Cas warily leaned back into his heels, his eyes staring into the window instead of looking around.

"We have a few hours before the appointment with your brother, and I have sent your work to you via email. Get on it." Dean said, walking back to his desk and sitting back down.

Cas wasted no time standing in shaky knees. He walked out of the office, hard, wet, and embarrassed. This was not a day to wear three layers of heavy clothing.

All through the morning Dean surprised Cas with different levels of pleasure. Even when he was asked to call Mr. Roman, he was on the highest setting.  A few times Mr.  Roman offered to call Dean to let him off for today since he sounded sick.

When it was lunch he was ultimately swept away from the office by Charlie, taking him out of the range of the vibrator. To which he silently thanked her for.

They are at a Chinese restaurant, Charlie telling him about what Anna did to Uriel in the break room, when he got a phone call from his brother.

"Hello?"

"Yes, hello? Is this Castiel Novak?"

The voice was not his brother, and the fact that a stranger had his brothers phone caused a slight panic.

"Ah-um yes? Who, may I ask, are you?"

The voice laughed awkwardly, "Ah yes, sorry my boss threw his phone at me and told me to call Cassie? Well he wanted to know.. what did you say?..." Cas looked at Charlie and put it on speaker he didn't want to be alone in this awkward situation.

"Ah oh yeah, what he wanted to know is what color suit you're wearing?! GABRIEL that is very inappropriate stop that! Sorry, excuse me for a second..."

A loud pop sound was heard and Charlie was holding in a laugh.

'Who the fuck is this guy?' She mouthed, Cas answered with a shrug.

"Where were we. Sorry it seems he wanted to know for matching purposes.  What color?"

"Um.. blue with a light brown trench?" Cas heard a scoff in the background and a 'when is he not wearing a trench coat?'

"Sorry for the interruption, we will be on time for the meeting with Mr. Winchester.

Another scoff, and a 'Mr. Winchester meet Mr. Win-' before the click signaling he was being hung up on.

"Well then.. that coffee meeting should be fun?" Charlie asked, thanking the waitress in Chinese before digging into the food this was set in front of them.

Cas just shrugged again. He doesn't know what the fuck his brother is doing, and by the sound of it he would be better off not knowing.


	10. Vanilla for a Pound of His Cake

**Summary for the Chapter:**

> Long story short. Dean's a tease.

After lunch Cas was back in the grasp of his boss. He was given another coffee when entering the floor.

 

"What's this for Mr. Winchester?" He watched Dean shrug and fiddle with the stapler on his desk. "I was just thinking about treating the meeting with your brother like a date, you know.. after the meetings over we can go out to dinner?"

 

Cas opened his mouth to tell him about Charlie's plans, but no words came out. He was distracted by how cute Dean was asking and a need to say sure was dancing on the tip of his tongue.

 

"Well, the meeting is in an hour and then at 4:30 you have a meeting over the phone with Matting. So... yes we can treat it like a date. But..." He cancel on any other plans with Charlie so he will have to tell him.

 

"Neato, but what?" Dean cocked his head to the side and gave a confused frown.

 

"I-I have a date with Charlie. Um. After work, so maybe we can schedule another date this weekend?" He scooted closer to Dean and patted his arm. Dean took it further and yanked Castiel slightly so he was falling into his arms.

 

"That's fine. As long as I get to spend some time with you before the week is out." Dean planted a soft kiss to Castiel's lips, and if that didn't make Cas weak in the knees.

 

"I'll be in my office. Call my chauffeur when it's close to time and we can go together." Then Dean was gone. Castiel's lips tingled with want. All he had left was an empty desk that his lover was sitting on, and a cooling coffee ordered with care.

 

He took a sip and sighed. Yup. This is perfect.

~~

 

It was time to meet his brother at the Cafe and to call him nervous was an understatement. If all goes wrong Gabe had all the power in the world to get Castiel's transfer in order. And if Dean fucks with the vibrator that is still in him, Gabe will definitely figure something out. Foreplay and sensual teasing has always been Gabe's forte, and his brother is practically an open book.

 

"Mr. Winchester?"

 

"Coming."

 

"Gadreel is waiting for us, in the lobby," Cas said packing his tablet and notepad in his suitcase.

 

"Lets hope this deal with Gabriel goes well." Cas muttered to himself.

 

"Yo Cas!" Dean called from inside his office. That voice sound a little too playful for Castiel's taste.

 

"Yes Dean?" He pushed through the doors and immediately stepped right back out.

 

"No."

 

"I refuse to even look at it."

 

"Aw come on Cas!" Dean's whiney voice made Castiel cringe. He open the door again and there stood Dean with a larger vibrating dildo in his hands.

 

"Where the hell do you get this stuff, may I ask?" Cas then shook his head. He remembers Deans countless other lovers that came in and out of the elevator. Of course he will have toys in his damn office. But then a thought flew into his embarrassing mind, that made his sick. Has he used that same one of someone else? Or does he switch out toys with every new lover that he has.

 

It's shape was more like a bunch of bubbles, an the light blue could match his eyes on a non cloudy day. Just the thought of eating dinner with his brother while his boss wouldn't hesitate to turn him into a needy mess, made his stomach ache.

 

"What do you say?"

 

"We..." Castiel cleared his throat, "we're going to be late sir."   
Dean shrugged the dildo was being turned on and off like the ticking of a clock. In the end, Cas walked over to Dean's desk and leaned forward, presenting to his boss.

 

"That's mighty sweet of you baby boy."

~~

 

Castiel was glad it wasn't them that was late. After a quickie Castiel and Dean still was there before Gabriel got there.

 

Seriously where was he? Dean tapped his shoulder, getting his attention before pointing outside the window, where his brother -albeit throwing himself in the arms of a large man- was standing.

 

The duo stepped through the front of the cafe, a chuckling Gabriel and a sighing secretary made their way to their table.

 

"Baby bro!" Both Dean and Gabriel call out when they are seated. Cas gave a small smile to Gabe only to turn his attention back to Dean's and his apparent brother's conversation.

 

"If this isn't the most awkward thing since the early 2000's," Gabriel cracked, earning a curt nod from his brother.

 

"Mr. Novak, meet my younger brother, Sam." Dean announced waving a polite hand towards the tall man by Castiel's brother.

 

"Funny, I didn't know you got into a secretary position." Dean smirked.

 

"Oh shut up, I don't have to suck everyone's privates just to meet a goal Dean," Sam rolled his eyes.

 

Dean only laughed. With a snap of a finger though, Mr. Winchester was back in business.

 

During the half hour that they had with Gabriel, Dean only switched the vibrator on three times. Cas squeaked halfheartedly in fear of being noticed by his brother that was blabbing nonstop about work.

 

The only time Cas was actually worried was when Sam shushed the table- and Dean quickly switched off the vibrator, automatically giving Castiel's prostate relief- to ask wha he was hearing. Dean jokingly blowing it off to his brother having fucked up hearing.

 

Cas didn't have to say anything. So the strain that kept him from bursting out of his seams wasn't pushed to the max. Which he was grateful for.

 

Most of the time Dean and Gabriel were discussing a form of new shipment that was more or less going to be connected with fellow companies in the district. All that Gabriel needed Sam or Cas for was for notes of dates and hours of certain meetings that they will be attending in the near future.

 

When all was said and done, Gabriel gave Castiel a hug, patting his butt lightly.

 

"Have fun," he muttered and walked off with Sam right on his heels. Castiel's cheeks burned the whole walk to the car, and the embarrassment didn't go unnoticed.

 

"What's got you all hot and bothered?" Dean murmured, a smirk playing on his lips.

 

"Gabe.. he must have known from the start," Cas said, his voice monotone, not willing to explain further.

 

"Hm. Well, no harm no foul."

 

Castiel felt a vibration in his jeans that, for once, was not the thing in his ass. He pulled out his phone and read the message aloud.

 

_"Don't forget to use protection, little secretary. I know I will. ;)"_

 

Cas face palmed while Dean on the other hand swerved the car in surprise. He turned and ripped the phone out of Cas's hand and reread the text.

 

"That son of a bitch is fucking my brother?!"

 

"Now hold on a minute," Cas tried, taking the phone back and pointing to the road, "pay attention. And maybe it's the other way around."

 

He shrugged, "Gabe has always been one to take ladies and fellas to his place, and even then he was a loud one." He chuckled, only to be interrupted by the sudden attack within him.

 

"Ah! Oh, Dean! I'm sorry I was just-Ohh shit- playing!" Castiel crossed his legs tightly, which only made the situation worse.

 

"Ah _little secretary_ , don't you know only I can play around like that." Cas bit his lip and refrained a heated growl towards the smirking man beside him.

 

The car jerked to a stop and Cas looked out the window. A damn hotel. Classic. But no room to complain when he's had a mess in his pants since 3:00.

 

"Shall we?"

 

"P-please?"

 

In the hotel room, it was silent. Aside from the squelching sound of Dean's fingers being up Castiel's ass. Cas was face down, half naked, and gagged with his tie once more. Arms held tight in Dean's other hand.

 

He huffed on the gag when Dean skillfully twisted his long fingers the right way, crossings his feet behind Dean's legs to keep from shaking out a much needed orgasm. He knows if he let it out now Dean will be upset.

 

"Cas, baby, you think you're ready?" Dean whispered against his clothed shoulder. A nod and a small press against Dean's fingers answered.

 

Dean teasingly rubbed his dick against Castiel's thigh, lathered it up with travel lotion and pushed into Castiel's waiting hole.

 

"You know," Dean moaned out, a high pitched grunt replied, "no matter how many times I fuck this ass, you're always tight." Dean continued, going a slow pace and enjoying the slow fuck.

 

Cas wasn't used to this, he never thought Dean was gonna be vanilla once with him, but here he is, whispering sweet nothings in his ear and praising the very body he claims to want to ruin with his cock.

 

Ruin. No amount of rough roleplaying will ever ruin him as much as this vulnerable slow sex. The kind of sex that leaves the submissive craving for more attention when they know they won't get it.

 

Dean's thrust came harder but still slow to pull out. Like he wanted his imprint to stick with Castiel's body longer. A hand wrapped tightly around Castiel's neck and lifted his face off the pillow into a position that left him choking on his own spit.

 

"Who do you belong to, Cas?" Dean asked still thrusting slow and hard. Cas couldn't speak with a full mouth, instead he just released muffled whimpers and met Dean's thrust every time. The slight tilt of his hips left him shaking.

 

"That right baby, fuck yourself on my cock. Like you fucking mean it."

 

Cas rocked his hips faster, his head tilted toward the ceiling, the overwhelming need to cum boiled in his lower belly.

 

He moaned into his tie, squeezing his thighs together before he could accidentally let it out.

 

"You think you can do it? You think you can cum from my cock?"

 

Cas knows he can do it. He's been waiting for permission and now that he's got it, screw being slow.

 

He held tightly onto his own sleeve, as he began thrusting harder than anything. Dean was only holding his arms now. Praises spilling out of his mouth like grains of sugar, and his grip like a vise on a stack of collectables.

 

He threw himself down on the mattress and convulsed as he came, his toes curled tight around Dean's thighs and that's when he felt the pool being released into his own ass.

 

Dean pulled out slow and yanked the gag off of Cas. He smiled, satisfied.

 

"Let's get cleaned up."

**Author's Note:**

> Sooooo how did you like it? Comments are welcome.


End file.
